HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → HCID 57336135, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate | HCID 2733207 | — |
| Reactant | HCID 17998717 | HCID 17998717 | — |
| Reactant | 6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid | HCID 66599213 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 57336135 | HCID 57336135 | 90.8% |
Reaction Steps
To a solution of 6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-nicotinic acid (500 mg, 1.6 mmol) in DMF (10 mL) were added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (569 mg, 1.8 mmol), N,N-diisopropyl ethyl amine (1.38 mL, 8.1 mmol) and 5,6,7,8-tetrahydro-(1,2,4)triazolo(4,3-a)-pyrazine hydrochloride (1.8 mmol). The resulting reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1 and then dichloromethane:methanol=9:1) afforded the title compound (605 mg, 86%) which was obtained as a white foam. MS: m/e=417.4 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08604062B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-08db31d808b54e9881b1154ad7b41ec3 |
| Source note | uspto-grants-2013_12 |